I love this update! We finally are almost finished with the starting Girls, the lifeguard is the only one without three hearts. This update was bigger than I expected.
To give help with one quest... the MC's mother will task him to find sleeping pills, to avoid searching aimlessly, just click on the guy who's married to the older lady that was pretty much unlocked early on. It'll say he'll have sleeping pills. If you click on him after having sex with his wife, you'll have to wait a day before entering their cabin and getting the pills.